Inquisitiveness for Dummies (or Aspergers patients)

Especially in your first meeting with a stranger, showing some interest in their life may lead to acquiring a new friend. Showing this interest without making them uncomfortable is tricky business.

The safest questions are easy, but also less interesting. "How are you" is usually OK. If you're at a gathering, something like "What's your connection to this crowd" is standard fare.

Another standard question, but more interesting, is "What do you do?" Although the question is phrased vaguely, its repeated use has changed its meaning to "What do you do for a living?" Some conversation experts advise against stating the question so directly, as it may lead to awkwardness if the stranger happens to be unemployed, or if the stranger is ashamed of what they do for a living. People working in prostitution, gambling, corporate law, the military, drug dealing, or AIG may be reluctant to discuss their work.

A good alternative to "What do you do" is "What keeps you busy?" This question has not yet come to mean "what is your job," and allows people to expound on what they do during free-time or evenings instead of their career, if they prefer.

Once a stranger has revealed what they do, either as a hobby or career, you can show interest by asking more questions on that topic. But don't take this too far. Questions that reveal the stranger's incompetence or lack of knowledge in their field will make them feel defensive. Don't ask a computer programmer to explain what the program they are trying to write is supposed to accomplish in the big picture if they seem like a nuts-and-bolts personality.

A generalization of the above examples is that you should avoid asking questions that "measure" people. Even something so simple as "where did you go to school" can lead to feelings of being measured. Those that got their degree a little community college such as "Pot State" may fear being measured as inadequate. A graduate of Harvard may feel like a fake for bearing such lofty credentials, or may fear being tested on their supposed smarts.

Other measuring questions include "What do your parents do for a living," "Do you have a car," "Does that job pay well," or "What was your SAT score?" Some of these may work well in special circumstances when the question is highly relevant to the topic at hand, but if you are unsure, just avoid asking these things.

For most good questions, you are able to state exactly why you want to know that answer to that, and how it was relevant to the conversation. Unstructured curiosity is a conversational weapon of incremental destruction.

It is best to discuss shared interests.